check-technologies - Tax & Payroll Operations Lead
Requirements
• 4-6+ years in payroll/tax operations • Demonstrated expertise in payroll tax operations/compliance (e.g., filings/remittances, notice resolution, corrections/amendments, reconciliations), and comfort owning tax decisions/tradeoffs. • Startup or high-growth company background. • Strong judgment and escalation instincts: knows when to self-serve vs. when to pull in the Tax & Compliance Manager / cross-functional partners. • Track record of process improvement: can spot patterns and help drive changes that reduce recurrence (tooling, documentation, controls). • Startup instincts in practice: writes the runbook before one exists, creates lightweight controls/visibility, and turns recurring issues into a scalable fix (not just a workaround). • AI-forward mindset: uses AI tools to move faster (analysis, drafting, pattern recognition) while validating for correctness in regulated work. • Strong communication skills. You can translate between team-level detail and leadership-level framing, and you know which audience needs which version. • A genuine learner. You'll be getting fluent in a niche domain on the job, and you find that interesting rather than uncomfortable. • Fintech or payroll platform experience is a plus (e.g., embedded payroll, payments, or compliance tooling). • TRAVEL & OFFICE POLICY • The Check team is distributed across the US. Roles can be remote, hybrid, or based in one of our offices in New York City or San Francisco. We offer ample opportunities and encourage employees to attend team offsites, events, and hackathons throughout year. All Checketeers gather in the spring for our annual 3-day company retreat. • For our in-office and hybrid employees, our offices are open all week. We provide meals on Tuesdays and Thursdays and there are regular happy hours, game nights, and other in-person events.
Responsibilities
• Own filing payment operations end-to-end within your scope (e.g., assigned jurisdictions): payment setup, verification, troubleshooting, and remediation when something goes wrong. • Diagnose and resolve complex tax notices, determining root cause across filings, payments, agency systems, and internal workflows. • Drive complex corrections and reconciliations (e.g., payment misapplies, reversals/reissues, under/overpayments), escalating thoughtfully when tradeoffs or risk are involved. • Partner with R&D / Product and cross-functional ops teams to inform system behavior and prevent repeat issues (better tooling, validations, automation, and documentation). • Identify patterns across payments + notices and propose improvements that reduce risk, shorten resolution times, and improve partner experience.
Benefits
• NYC, SF, LA, Seattle$120,000 – $137,500 • Offers Equity • Remote US$102,000 – $117,250 • Offers Equity • The actual annual salary for this role is dependent on each candidate’s experience, qualifications, and work location. Most new hires are placed near the midpoint of this range to ensure fairness with our existing team’s compensation. • Check is proud to offer employee benefits that support a healthy life outside of work for individuals of all backgrounds. Full-time team members have access to flexible PTO and sick leave, generous paid parental leave for all new parents and flexible return-to-work, a 401k retirement plan, and a $100 monthly stipend for home internet and mobile phone expenses. We also provide high-quality medical, dental, vision, short-term/long-term disability, and basic life insurance coverage, effective on your first day of work. • Upload your resume here to autofill key application fields. • Drop your resume here! • Parsing your resume. Autofilling key fields... • or drag and drop here • I prefer not to answer • Another Gender Identity • Heterosexual / straight • Asian or Asian American • Black or African American • Hispanic or Latine • Indigenous or Native American • Native Hawaiian or Other Pacific Islander • Person with disability • Refugee or immigrant • None of the above • Check may use Artificial Intelligence with this application. Learn more.
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